The Role

• Provide day-to-day project leadership following structured SDLC methodologies like agile and waterfall throughout the project lifecycle including project definition and approval, project plan development, project execution, progress monitoring
• Foster continual improvement in project delivery by enthusiastically collaborating with co-workers to share ideas and opinions about improving processes, services and customer experience
• Drive and motivate the project team to achieve results, resolve conflicts, and escalate issues as needed
• Works with line of business leaders to define, prioritize, and develop projects and programs
• Coordinate with the business owners and IT to collect business requirements and develop workflows, ensuring project deliverables are aligned with organizational policies and any external regulatory compliance requirements
• Develop and execute the project communications plan including communications and presentations to executive leaders and end users
• Partner with business owners and project sponsor to ensure smooth project go-live, resolving roadblocks and managing escalations as required
• Develop and manage effective relationships with third party vendors and service providers to ensure successful delivery per the vendor contract or internal design documentation
• Monitor user adoption and project success via KPIs and report progress to project sponsor and management
• Develop training and performance support strategies to reinforce new processes and to ensure rapid deployment and project success
• Oversees the work of project management staff and coordinates resources

About You:

• 7+ years experience as a project manager, managing full life cycle, enterprise wide technology projects
• Proven track record of meeting project timelines, budgets and quality with both internal and external resources
• Proven ability to work cross-functionally at all levels of the organization to deliver results, leveraging strong influencing skills in a matrixed project environment
• Good technical understanding, with the ability to translate business requirements into technical requirements
• Ability to accurately gauge time and resources required to meet functional and technical requirements
• Ability to demonstrate creativity in solving problems or generating improvement ideas
• Ability to prioritize competing or conflicting requests
• Ability to work effectively and professionally with employees at all levels of the organization
• Excellent presentation, written and verbal communication skills
• Effective interpersonal skills and ability to work in a team environment
• Enthusiastic, customer focused, service oriented, self-starter
• Strong people leadership skill
• Required – Bachelor’s degree (Business Administration, Information Systems) or equivalent.
• Preferred – PMP, CAPM, Agile or ITIL certification

About Pilot

Pilot launched in 2017 to bring the back office into the modern era. Pilot provides small businesses with dedicated finance experts - which Pilot hires as full-time, U.S.-based employees - who learn the ins-and-outs of their business. Pilot integrates directly with the billing, banking, expense, and payroll systems customers already use. With a special blend of custom software and expert bookkeepers, Pilot delivers accurate, consistent bookkeeping and financial management and tax services that give entrepreneurs the freedom to focus on their business.

Pilot has over 1,000 customers and has raised over $170 million in financing from Sequoia, Index Ventures, Stripe, Bezos Expeditions, and Whale Rock. Our investors also include a long list of world-class entrepreneurs, including Patrick and John Collison, Drew Houston, and Diane Greene. Our most recent funding round doubled our valuation to $1.2 billion – Meet Fintech’s Newest Unicorn.

Why Pilot?

• We invest in our employees’ development and happiness because our employees are the keys to our success and ensuring happy customers
• The opportunity to join a seasoned founding team that has led companies through two prior successful startups and acquisitions (by Oracle and Dropbox).
• Flexible vacation/time-off policy
• All federal holidays are observed
• Competitive benefits package including wellness benefits such as Modern Health, Headscape, One Medical, Aaptiv and Rightway
• Parental leave for birthing or non-birthing parents – 100% pay for 12 weeks
• 401(k) plan

Pilot commits to provide a work environment free of discrimination and harassment, as well as equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status. We also consider qualified applicants regardless of criminal histories, consistent with legal requirements. You may view all of Pilot’s recruiting notices here, including our EEO policy, recruitment agency policy, recruitment scam notice, and important E-Verify information.